I grew up in Chicago and still visit frequently and after traveling the world, it still remains my favorite city. Here is a list of my 25 top things to do in a Chicago.
Luka Parker said it best when he sang “My Kind of town Chicago is”. In the “Windy City”, there is a wide range of sights and things to do in Chicago for all interests. Here is my list of the top 25 Chicago attractions in my favorite city.
I grew up in Chicago and spent my formative years there. Even though I have been away for half my life now, I still think of it as home and go back to visit a few times each year. There is always plenty for me to do and see on my visits, whether it’s going back to some of my favorite sights or trying something new.
For the visitor, Chicago is an easy destination to tour. I can easily get from the airport to the downtown “Loop” area on inexpensive public transportation. Then, many of the most popular attractions and best things to do in Chicago are all within walking distance.
Quick Answer
The best things to do in Chicago include taking an architecture river cruise, exploring Millennium Park and Cloud Gate, walking the Chicago Riverwalk, visiting the Art Institute of Chicago, enjoying Navy Pier, and seeing the skyline from a famous observation deck. You can also explore local neighborhoods, relax along Lake Michigan, try Chicago-style food, visit museums, and experience live music or nightlife. For first-time visitors, 3–5 days gives you enough time to enjoy Chicago’s major attractions while discovering a few local favorites without rushing.
How to get from the Chicago airport to downtown
Chicago’s O’Hare airport (ORD) is about a 30-minute drive from downtown under good traffic conditions on I-90 (which isn’t often). I can take a taxi or a ride-share vehicle, but it is just as easy to take the train from the airport into the city.
The Blue Line train terminus is at O’Hare Airport. I follow the well-marked signs to get from baggage claim to the station. I can buy a one-way ticket at one of the kiosks or use my tap-and-pay credit card to go through the turnstiles.
Chicago’s Blue Line has undergone a recent multi-million dollar renovation, which means the stops along the route are clean, well-lit, and accessible. Depending on where I am staying downtown, I may want to change trains at the Clark/Lake or State/Lake stops to one of the other lines if I don’t want to walk a few extra blocks.
If I am flying into Chicago’s Midway Airport, then I take the orange line into downtown, which terminates at this airport. I use this handy CTA map to help you navigate.
Where to stay in Chicago
Chicago has a dizzying array of accommodation options, especially in the downtown area. The choice depends on my budget, the types of services I want from a hotel, how much space I need, and the location.
There are historic options like the Drake Hotel (where I have stayed a few times), the Palmer House, or the Blackstone. There are also many new high-end choices, as well as many less expensive chain hotels.
I like to stay in the downtown-loop area so that I don’t have to spend as much time in transit. If the majority of the activities I want to do are along the lakeshore, then I stay within walking distance.
It’s about a 3-mile walk from the north end of downtown at Oak Street to the Adler Planetarium on the south end of the museum campus. Staying at a hotel near the Chicago River or Millennium Park will put me midway and make it easy to walk to the majority of the tourist sights.
How long should you stay in Chicago
Ideally, I would recommend staying in Chicago for no less than 4 days, though I like to stay longer when I can. There is no lack of good things to do in Chicago for any length of time.
The museums are world-class and deserve at least a half day each. I like to stroll the Magnificent Mile and explore Navy Pier, look out over the city from one of the signature skyscrapers, take in a show, and have a few good meals.
In 4 days, I can explore the heart of the city and enjoy it at a leisurely pace. To see sights beyond the downtown area, like the Frank Lloyd Wright studio and houses, Wrigley Field, or the Museum of Science and Industry, it will most likely take more time. I recently spent a week in Chicago playing tourist, and did not get to do everything on this list.
Things to do in Chicago in the Downtown-Loop area
Now to decide what to do in Chicago. My list of 25 fun things to do in Chicago includes many of the most popular and “must-see” sights, as well as some of the ones that I think make Chicago unique. Actually, narrowing down this list to just 25 was a challenge (there will need to be a part 2 to this list at some point).
Adler Planetarium
I escape our planetary confines for a little while as I explore the universe in the US’s first planetarium, which was built in 1930. The Adler Planetarium is one of the three museums that make up the Museum Campus. Many great exhibits span all aspects of stargazing and exploration. Growing up, seeing a star show here on a school field trip was one of my most memorable museum experiences.
Buddy Guy’s Legends Bar
Chicago Blues music had a big influence on the evolution of early Rock and Roll. One of the easiest and most pleasant ways to experience Chicago Blues music is to spend an evening at Buddy Guy’s Legends Bar in the South Loop.
360 Chicago
For a short time after it was built in 1968, the 100-story John Hancock Center was the second-tallest building in the world and the tallest skyscraper in Chicago. While it has long lost those titles, it remains my favorite tall building in the city’s skyline.
As the name implies, the 360 Chicago experience provides impressive views in all directions. My favorite view of the Chicago skyline is from the top of the John Hancock Building.
Chicago Art Institute
I go to the Chicago Art Institute to see a world-class collection that spans 5000 years of human creativity. I love impressionism, so I plan to spend quite a bit of time here studying the many works by Monet, Cezanne, Renoir, Van Goh and others. I like to go early or just before closing to avoid the crowds.
Chicago Cultural Center
Across the street from the Cloud Gate sculpture is another historic Chicago building, the Chicago Cultural Center. I go in to take a peek at the world’s largest Tiffany stained glass dome and at all the beautiful inlaid marble surrounding it. The Cultural Center also offers many free performances all throughout the year.
Chicago River Architecture Tour
Chicago is known for its photogenic lakefront skyline and unique and diverse architecture. The 1871 Great Chicago Fire laid waste to most of the city, which then created an opportunity for creative new buildings to rise up out of the ashes. Experimentation and innovation became the standard and resulted in some of the world’s tallest buildings at the end of the 19th century.
One of the best ways to see Chicago’s unique and diverse historic architecture is on a Chicago River architecture boat tour. There are many to choose from, but I like the one offered by the Chicago Architecture Foundation aboard the Chicago First Lady. They offer fun and in-depth commentary describing the history of the many buildings, both old and new, as I cruise up and down the Chicago river.
Another cruise that I really enjoyed was the combination river and lake cruise offered by Wendella. I chose an early evening cruise in the summer and watched the sun set over the city as we cruised through the locks and onto Lake Michigan. On the way back, I got to see the beautiful Chicago skyline all lit up at dusk.
Chicago style pizza
Chicago pizza is a true pie – deep and loaded with sauce, cheese, and other goodies. There are two types of Chicago pizza: deep dish and stuffed. The deep dish is the most common and is made like an open-topped pie. There are a number of good Chicago style pizzeria’s in the downtown area, though I know I can’t go wrong with the original Pizzeria Uno, where deep dish pizza was invented, or its sister spot, Pizzeria Due.
The less common but equally delicious Chicago original is the stuffed pizza. This starts with a layer of dough, then lots of mozzarella cheese, which is topped with another layer of dough. Then the sauce and other toppings are added. Giordano’s is one of my favorites for stuffed pizza, and there are a number of locations within the Chicago Loop.
Chicago Theater
There is the historic Chicago Theater building, and then there is also the wonderful Chicago theater scene, which I think is on par with Broadway in New York City (I’ve experienced both).
The Chicago Theater was built in 1921 for 4 million dollars as the first lavish movie theater of its kind. The interior details were inspired by the Royal Chapel at Versailles and the Paris Opera House.
In 1985, the theater was saved from demolition and was fully restored to its original grandeur. Today, I can attend performances by top-name artists. The theater also offers a tour to learn all about the history and architecture of this beautiful venue (or why not do both).
For other performance options, Chicago has something for all tastes and budgets (discover what’s playing at Chicago-Theater.com). In the heart of downtown, the Chicago Theater District offers the best of Broadway productions in some of the country’s most historic theaters, but without the New York prices.
When Hamilton was playing in Chicago, I was able to get last-minute tickets at a fraction of the cost of a seat in New York. There is also a tour of the best historic theaters to learn more about these beautiful buildings from the early part of the 20th century.
Field Museum of Natural History
The Field Museum is one of the three museums in the South Loop’s Museum Campus. As one of the largest natural history museums in the world, there is plenty of material for all interests. There are instructive dioramas, Egyptian mummies, and lots of pretty samples of interesting rocks. And, of course, there are also dinosaurs – in fact, the museum has the largest skeleton of a T. rex ever discovered (named Sue).
Magnificent Mile
It’s fun to stroll and window shop on Chicago’s Magnificent Mile, which really is a mile long and extends along Michigan Avenue from Oak Street on the north to the Chicago River on the south. The avenue is lined with high-end shops like Tiffany, Cartier, and Dolce and Gabbana. There are also high-end accommodations like the Ritz, the Four Seasons, and the Peninsula hotels.
There are also some historic landmarks along this mile, with the Chicago Water Tower being one of the most important. It was built just two years before the Great Chicago Fire and is one of the few buildings that survived the devastation. Today, the Water Tower is used as an art gallery that showcases the works of local photographers and artists.
My favorite time of year to walk down Michigan Avenue is during the Christmas holiday season. Over a million lights decorate the trees that line the street, and the shop windows are colorfully decorated for the holidays.
Marshall Fields (now Macy’s)
The 13-story flagship store for Marshall Field and Co. was built in the early 1900’s, takes up a whole city block, and is still the third largest store in the world. Among the architectural details of this historic landmark is a shopping atrium topped by a 6000 square foot vaulted glass dome mosaic made by Louis Comfort Tiffany using 1.6 million pieces of iridescent glass.
Besides its large size, the store also established many shopping “firsts” that we now take for granted: the first store to use escalators, the first to set up a bridal registry, and the first to provide revolving credit. It was also the first to establish a department store tea room, which still exists today as the Walnut Room restaurant. This is a good spot for an affordable lunch in historic surroundings, especially at Christmas when the traditional 45-foot tree decorates the restaurant.
Before I leave, I make sure to buy a box of Frango Mints, a Marshall Fields classic since 1929.
Millennium Park
Millennium Park and its Cloud Gate (aka The Bean) sculpture have become one of the most popular sights in Chicago. The photogenic reflective metal art piece is a big draw for selfie photos, but the park also offers other fun sightseeing opportunities. Summer concerts – some free-can be enjoyed at the Jay Pritzker Pavilion, and on hot summer days, the Crown Fountain is a fun place to play and cool off.
Navy Pier
The pier was built in 1916 and was named in honor of the naval veterans from WWI. The naval connection continued when the pier was used by the US Navy as a training center during WWII. Today, the revitalized Navy Pier is a multi-use, popular Chicago destination with lots of restaurant options and activities for the whole family.
The Chicago Children’s Museum entertains the youngest family members, while the Chicago Shakespeare Theater appeals to the older crowd, and the iconic Ferris wheel is fun for all ages. During the summer, Navy Pier puts on a fireworks display a couple of times a week, and during the Christmas season, I like to check out the Winter Wonderfest.
Palmer House
The Palmer House is another one of Chicago’s great historic hotels, which is now part of the Hilton collection. It was the first hotel in the city to have elevators and the first hotel to provide light bulbs and telephones in its guest rooms.
I like to come here for a happy hour drink in the lobby bar under the highly decorative frescoed ceiling or take in afternoon tea at the Lockwood Restaurant. I never miss one of their brownies, which were invented in the Palmer House kitchens specifically for the 1893 Columbian Exposition World’s Fair.
Shedd Aquarium
The Shedd Aquarium, the third museum in Chicago’s Museum Campus, is my favorite of the three and is one of the best things to do in Chicago with kids. It was built in 1930, and for a long time, this 5-million-gallon aquarium was the largest in the world.
I never tire of walking through the classic galleries looking at the realistic underwater habitats from the Caribbean or the Amazon. It’s a popular attraction with locals as well as with tourists, so it can get quite busy. I try to get there when it first opens to avoid the crowds.
Street art
hicago has invested in accessible public street art since the first big sculpture was installed by Picasso in 1967. Since then, many other sculptures by famous modern artists have been installed in the downtown area.
The south Loop around Columbia College is also a showcase for many fine murals. I describe my street art discoveries in my post The Best Chicago Street Art – Finding Murals, Sculptures and Other Public Art in the Windy City
Willis (Sears) Tower
I will always think of it as the Sears Tower, even though it was renamed to the Willis Tower in 2009. When the 110-story building was completed in 1973, it became the tallest building in the world, a record held for almost 25 years. The Skydeck on the 103rd floor offers an interesting observation experience: The Ledge.
The Ledge is an all-glass box that juts out from the side of the building and gives an unobstructed view of the street below your feet. This is a very popular attraction, so I went early in the morning before it got too busy. For those not afraid of heights, this is certainly one of the coolest things to do in Chicago.
Things to do in Chicago, a little further afield
Chicago History Museum
Located at the southern end of Lincoln Park, the Chicago History Museum has been preserving and interpreting Chicago history since 1856. This was a fun museum to visit and learn about Chicago’s past. The collection is huge (about 22 million items), presenting both permanent exhibits and rotating exhibits with varying themes.
Take yourself out to the ball game
When you consider that the city is home to two baseball teams – the Chicago Cubs, who play at historic Wrigley Field, and the Chicago White Sox, who call Rate Field home – a baseball game is a must. But the most unexpected delight in town? Catching a Chicago Bandits AUSL game at the Stadium at the Parkway Bank Sports Complex. Tickets are very affordable and easy to get, and as Bandits pitcher Odicci Alexander recommends, “definitely be ready to support women’s sports loud and proud.”
The rest of the year, it’s easy to see a variety of sporting events with top-tier athletes. Football fans can go to a Chicago Bears game, while basketball lovers can see the men’s Chicago Bulls and the women’s Chicago Sky basketball teams. And don’t forget Chicago Blackhawks hockey, the Chicago Fire FC men’s soccer and the Chicago Red Stars women’s soccer. It’s safe to say Chicago is a sports town. On any given day, you’ll find a sporting event happening, with fans filling arenas, stadiums and bars to root for their favorite players.
See iconic architecture on a river cruise
Taking a cruise along the Chicago River is a wonderful way to see the skyline and learn about this vital urban waterway. One of the most popular options is the one operated by the Chicago Architecture Center that offers a fascinating insight into the construction and history of some of the city’s most iconic buildings. You don’t need to be an architecture buff to enjoy this trip down the river – expert guides share wonderful stories about the history and culture of the city, and the people responsible for its growth and progress.
Planning tip: This is routinely voted as the best boat tour in the US, and tickets get snapped up quickly, especially during peak season. Book in advance to avoid disappointment and arrive 30 minutes before your sailing time.
Dive into Chicago’s cocktail scene
The Violet Hour is said to be the birthplace of craft cocktails in Chicago, and no visit to the city is complete without a drink at this OG speakeasy. If the yellow light is on, it’s open. Step through velvet curtains and into an upscale cocktail bar from a different era. Be sure to keep your phone on silent and dress smartly to ensure admittance.
But competition is fierce for the title of the ultimate cocktail experience in Chicago, and The Aviary, which offers complex molecular drinks alone or paired with small plates with complex presentations, offers stiff competition. It’s part of the Michelin-starred Alinea Group, and so is The Office speakeasy below it.
If you can’t get enough of Chicago’s speakeasies, add The Drifter and Lady Bird to your list. The Drifter is located on the lower level of River North’s iconic Green Door Tavern, the city’s oldest drinking hole. Find the entrance en route to the bathroom behind a bookshelf. And the best part? There’s live entertainment nightly from Wednesday to Saturday (expect to pay a cover). Lady Bird is nestled in the basement of the Hoxton, in the West Loop. The low-lit bar features live music (jazz, soul and rock) Thursday through Saturday and evokes feelings of 1960s glam.
Shop local in Chicago’s cool neighborhoods
Chicago is a vibrant collection of neighborhoods. To really experience the city like a local, go beyond the Loop, avoid Michigan Ave and support local neighborhood stores that reflect the city’s diverse makeup.
Andersonville sits on the North Side and has intriguing Swedish roots. The Clark St passage between Foster and Bryn Mawr is littered with nostalgic shops that give off Wes Anderson vibes, while Wicker Park and Bucktown tailor their scenes to local hipsters and young families.
End your retail tour in Hyde Park, home to Michelle and Barack Obama (when they’re in Chicago). The Silver Room is a must – this Black-owned store features various products that put Black culture and Black artisans in the spotlight.
Find Chicago’s magic
Some of the most prominent magicians in the industry reside in Chicago, and it’s no wonder the city has become a hub for a burgeoning magic scene.
In the Loop, spectators can get dolled up for an intimate night of magic with Dennis Watkins, a third-generation magician, at the opulent Palmer House Hilton – dress well, as cocktail attire is encouraged.
If you prefer something more laid-back, head north to the Chicago Magic Lounge. In true magical fashion, the entrance is disguised as a laundromat. Step through the portal to find a host ready to guide you to a show or the bar, where the bartenders serve up close-hand magic alongside delicious drinks.
Groove to live blues and rock
No musical genre is as closely tied to Chicago as the blues – the electric blues, to be more precise. When Muddy Waters and friends plugged into their amps in the 1950s, guitar grooves reached new decibel levels, and the Chicago blues scene was born.
You can still hear the real deal in clubs around town, such as Buddy Guy’s Legends, where the icon himself takes the stage every January, or Rosa’s Lounge, where the vibe is a bit more down and dirty. Held in Millennium Park in June, the Chicago Blues Festival attracts top talent.
Planning tip: The blues paved the way for rock and roll, and you’ll find cool little venues hosting edgy indie bands on many a street corner. Thalia Hall, Hideout and Reggies are good places to start.
Dine at award-winning restaurants
Over the years, Chicago’s reputation as a culinary destination has flourished thanks to local chefs such as Grant Achatz, Rick Bayless, Stephanie Izard, Erick Williams, Bill Kim and Carlos Gaytan. For high-end dining, head to the West Loop and take your pick of top culinary artists, Beard winners and Michelin-starred chefs.
Joe Flamm’s Rose Mary, an Italian-Croatian restaurant, is one of the city’s hot spots, Gibson’s Italia serves perfect Florentine steaks to the power dining crowd, and The Publican delivers top-notch brunch. Classics that wow include The Girl & The Goat and Frontera Grill. Head to Hyde Park for James Beard award-winning new Southern cuisine at Virtue, an Obama favorite.
“At Carmine’s, you can’t go wrong with a big pasta dish to share,” says Chicago Bandits pitcher Odicci Alexander. “It’s that classic comfort, family-style vibe that always hits after a long day in season.” Carmine’s has locations both in Chicago and Rosemont, near the Bandits’ stadium.
“I’m always getting tacos at Cilantro, too,” Alexander says. “It’s simple, fresh and full of flavor. It’s one of those easy spots that never disappoints when you just want something quick but good.”
To celebrate a special occasion, book a reservation at Grant Achatz’s restaurant Next, where the concept, decor and menu change completely a few times a year.
If you’re visiting Chicago on a budget, head to the Athenian Room in Lincoln Park for the chicken kalamata (a Tina Fey favorite). Lou Malnati’s Pizza makes the city’s favorite deep dish pies. Try Oasis in the Loop for Lebanese fare or Aguascalientes in Little Village for Mexican fare.
Make the most of Millennium Park
In the playful heart of Chicago, Millennium Park shines with whimsical public art. Go ahead, walk under Anish Kapoor’s Cloud Gate – aka “the Bean” – and touch its silvery smoothness. Let the human gargoyles of Jaume Plensa’s Crown Fountain shower you with water to cool down in summer or unfurl a blanket at Pritzker Pavilion, the Frank Gehry-designed swooping silver band shell, as the sun dips and gorgeous live music fills the twilight air.
Planning tip: Check out the schedule of free summer concerts from June to August – jazz and world music on Mondays and Thursdays and classical music on Tuesdays, Wednesdays, Fridays and Saturdays.
Take a Windy City tour
Want to know all of the city’s history and secrets? Take a guided tour with a renowned local historian to uncover lesser-known facts and all sorts of insider information that will help you win Trivia Night back home.
Sherman “Dilla” Thomas is a wonderful advocate for his home city, and there ain’t nothing about Chicago that this man doesn’t know! His company, Chicago Mahogany Tours, leads walks and bus tours through the city’s neighborhoods and imparts fascinating insight into the history and people that keep the Windy City thriving.
Planning tip: These tours book up fast – book well ahead of your arrival in Chicago to ensure you snag a spot.
Stroll along Navy Pier
Stretching away from the skyline and into the blue of Lake Michigan, the half-mile-long Navy Pier is one of Chicago’s most visited attractions. Its charms revolve around the cool breezes and sweet views, especially from the vertigo-inducing, 196ft-tall Ferris wheel. High-tech rides, splash fountains, big boats and sugary snacks blow the minds of young ones.
Live music, Shakespearean theater and whopping fireworks displays entertain everyone else. A smart renovation has added public plazas, performance spaces, art installations and free cultural programming.
Discover African American History at the DuSable Museum
The DuSable is the oldest independent African American museum in the United States. It tells the story of the Black American experience through notable people and events.
Exhibits have celebrated Chicago’s first Black mayor, Harold Washington, showcase art collected by the publisher of Ebony and Jet magazines, and offer scenes from the civil rights movement. Since it’s a nonprofit museum, admission is free, though donations are appreciated.
Get cultured at the Art Institute
The Art Institute of Chicago is one of the most beloved places to visit for locals and the city’s top attraction for visitors. Even if you have just a couple hours to spare, a visit is well worth your while.
The museum features many famous paintings, including modernist works by Mondrian and Georgia O’Keeffe, as well as dreamy impressionist paintings by Monet and Matisse. If the weather is warm, take a break in the garden cafe before going back to join one of the free art workshops or tours. Be sure to snap a souvenir photo by one of the lions that guard the front entrance.
Laugh out loud at local comedy shows
A group of jokesters began performing intentionally unstructured skits in a Chicago bar a half-century ago, and voilà – improv comedy was born. Located in historic Old Town, the Second City still nurtures the best in the biz, though several other improv theaters also work from booze-fueled suggestions that the audience hollers up.
Among the city’s 200 theaters are powerhouse drama troupes such as Hollywood-star-laden Steppenwolf, the Black Ensemble Theater and heaps of fringey, provocative “off-Loop” companies, such as The Neo-Futurists.
Frank Lloyd Wright Studio tour
Frank Lloyd Wright is considered the father of the Prairie school of architecture and is one of the best-known American architects. I took a short drive to the suburb of Oak Park to see a large concentration of houses designed by Frank Lloyd Wright. This was also where I toured his home and studio.
For an overview of the architect’s life and work, I started with a Frank Lloyd Wright Home and Studio tour given by guides from the Frank Lloyd Wright Trust. A map for a self-guided walk around Oak Park lets you see some of his many buildings, including the Unity Temple.
I spent half a day here, though I could easily have spent a full day by taking more than one of the tours. To get here by public transport, I took the green subway line west to the Oak Park station.
Garfield Park Conservatory
The Garfield Park Conservatory is one of the largest in the country. The eight different gardens under glass make a great escape during the cold and drab winter months. I was also attracted by the permanent installation created by glass artist Dale Chihuly.
The first of Chihuly’s garden series was displayed here in 2001, titled “Chihuly in the Park: A Garden of Glass.” The Persian Lilly Pads, which were displayed at this exhibition, were purchased by the Garfield Park Conservatory and are now on permanent display.
I easily reached the conservatory using the green subway line to the Conservatory-Central Park Drive stop.
Lincoln Park Zoo
Since its founding in 1868, Lincoln Park Zoo has been free to visit. I’ve been visiting the zoo since I was a child, and I never tire of seeing my favorite exhibits. I especially love seeing the polar bears, the penguins, and the gorillas. The Farm-in-the-Zoo is also a fun experience for kids.
The zoo is in Lincoln Park, about 3 miles north of downtown. I can take a bus to get there, but I find it easier to use one of the ride-share options. Alternatively, a visit to the zoo is easy while biking the Lakeshore Trail.
Museum of Science and Industry
With a little more time, a trip to the Museum of Science and Industry is well worth it. The museum is not the easiest to get to using public transportation, so I usually get there with a taxi or ride-share.
Among the unique interactive exhibits, I like the full-sized replica of a coal mine, the German submarine U-boat captured in WWII, and the command module of Apollo 8. I also never tire of seeing the miniature fully decorated and furnished fairy tale castle.
My favorite time of year to visit is at Christmas time, when the museum celebrates Christmas Around the World with 40 decorated trees that represent different cultures around the world.
North Avenue Beach and the Lakefront Trail
I spent my teenage summers hanging out at the lakeshore beaches. Chicago has many of them, and each has its own personality. Each local has their favorites. Oak Street beach, which is right on the northern edge of downtown, is the “it” beach to see and be seen.
But to experience a beach more like a local, I rent a bike and pedal my way for about a mile north along the Lakefront Trail to North Avenue Beach, located at the southern end of Lincoln Park. (I rented my bike at one of the many bike rental kiosks across the street from the Drake Hotel.)
An ocean liner-inspired beach house is one of the fun features at North Avenue Beach. There are a couple of dining choices and food concessions here, including an ice cream shop. There are also rental options for lounge chairs and umbrellas, bikes, wakeboards, and paddleboards. My favorite thing about this beach, though are the fantastic views of Chicago’s downtown.
Second City Comedy Club
The Second City comedy theater has been a fixture in Chicago since 1959. Many well-known comedians are alumni, and quite a number have moved on to performing on the equally long-running Saturday Night Live TV program (think Dan Aykroyd, Bill Murray, Mike Meyers, and Tina Fey).
An evening performance includes scripted material as well as a lot of improv based on audience suggestions, so you never know what you are going to get. As a result, each show is always different and always fun.
I get to the Second City Theater on the blue or brown subway lines and get off at Sedgwick.
Wrigley Field
For baseball fans, catching a game at the historic Wrigley Field is a must. The stadium was built in 1914 and is listed as a National Historic Landmark. Unlike more modern baseball stadiums, though, Wrigley Field sits in the middle of a residential neighborhood and has no big parking lots. The easiest way to get there is via the red subway line to the Addison station, which lets you out one block from the stadium.
There is also a fun and informative behind-the-scenes stadium tour.
When is the best time to visit Chicago?
Pretty much any time of year is a good time to go because there is always something interesting to do and see. Winters in Chicago get a bad rap, but if I want to tour Chicago on a budget, that is actually the best time to go and save some money.
What are the best things to do in Chicago?
Start with an architecture river cruise, Millennium Park, the Art Institute of Chicago, Chicago Riverwalk, Navy Pier, and one local neighborhood such as Wicker Park, Pilsen, or Andersonville. Current travel guides also recommend sports, live music, food, and Chicago’s famous cocktail scene.
What are the best things to do in Chicago in summer?
Summer is ideal for lakefront beaches, outdoor festivals, river cruises, baseball games, Millennium Park events, neighborhood festivals, and waterfront walks. Chicago’s official tourism site currently highlights major free summer events, concerts, outdoor movies, and lakefront activities.
What are the best things to do in Chicago for young adults?
Young adults can combine an architecture cruise, West Loop dining, Wicker Park, live music, rooftop views, sports, beaches, and Chicago nightlife. Exploring neighborhoods beyond the Loop also gives the trip a more local feel.
What are some unique things to do in Chicago for adults?
Try a Chicago Magic Lounge show, neighborhood tour, blues club, architecture cruise, local cocktail bar, or lesser-known neighborhood. These experiences go beyond the standard tourist checklist while still showing Chicago’s culture.
What are some unique things to do in Chicago for couples?
Couples can take a sunset river cruise, walk the Riverwalk, enjoy skyline views, explore an atmospheric neighborhood, visit a rooftop bar, or spend an evening listening to live blues.
What are the best free places to visit in Chicago?
Great free options include Millennium Park, Lincoln Park Zoo, lakefront beaches, Chicago Cultural Center, neighborhood walks, and seasonal festivals. Free museum days and outdoor concerts can add even more value depending on your dates.
What are the top tourist attractions in Chicago?
Popular Chicago attractions include Millennium Park and Cloud Gate, the Art Institute of Chicago, Navy Pier, Willis Tower, the Chicago Riverwalk, and architecture cruises. First-time visitors can see many of the highlights in two or three days.
How many days do you need in Chicago?
Three to five days is ideal for most first-time visitors. Two or three days can cover the major attractions, while extra days give you time for museums, neighborhoods, food, nightlife, and the lakefront without rushing.
Final Thoughts
Chicago is a city that mixes iconic attractions, local neighborhoods, lakefront views, world-class museums, food, nightlife, and unique experiences in one trip. First-time visitors should prioritize highlights like the Chicago Riverwalk, architecture cruise, Millennium Park, Art Institute of Chicago, Navy Pier, and a few local neighborhoods.
The best trip does not come from trying to see everything. Choose activities in Chicago that match your travel style, leave time for local food and relaxed walks, and keep some flexibility for seasonal events. Whether you visit for a weekend or several days, Chicago offers enough variety to make every trip feel different.
